Onboarding

The first two weeks for a new team member.

Before day 1 (hiring manager)

• Create Slack account and add to all relevant channels
• Create GitHub account (if technical role) and add to org
• Provision Handbook access via Cloudflare Access
• Set up Google Workspace account if applicable
• Add to 1Password / Bitwarden vault
• Schedule welcome call (day 1)
• Assign a buddy (someone outside their direct reporting line)

Day 1

• Welcome call with Ray + hiring manager
• Handbook tour — start at the home page and read at your own pace
• Required reads before end of day:
  • Remote collaboration
  • Maintainer guide
  • Their role-specific onboarding (see below)
• Join #general, location channel, and role-relevant channels in Slack
• Intro post in #general — name, location, role, something personal

Week 1

• 30-min 1:1 with buddy, every day
• 30-min 1:1 with manager, end of day 1 and end of week 1
• Shadow a live customer ticket or order (even non-CS roles)
• Skim every major handbook section
• First small task completed — something that touches the real system, not a simulated exercise

Week 2

• First independent task (something that would have gone to someone else)
• 1:1 with Ray — ask anything
• Provide feedback: what’s unclear in the handbook? What’s missing? Actually update it.

Role-specific onboarding

Customer service

• Day 1: shadow an agent through 5 tickets
• Day 2: answer tickets with full supervision
• Day 3: answer tickets with spot-check supervision
• Day 5: independent, with escalation as needed

Engineering

• Day 1: local dev environment set up, can run OMS locally
• Day 2: make a trivial PR (typo fix / dev doc update) to practice the workflow
• Day 3: pick up a real small task from the backlog
• Week 2: shipping features

Operations

• Day 1: shadow an end-to-end order flow
• Day 2: supplier portal tour
• Day 3: first reconciliation or report

30-day check-in

At 30 days, manager and Ray run a joint check-in. Topics:

• What’s going well?
• What’s harder than expected?
• Any handbook gaps you’ve found?
• Is the role what you expected when you signed on?

This is a two-way evaluation. If something’s not working, better to surface it early.